Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025809/ez2077sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025809/ez2077Isup2.hkl |
CCDC reference: 290195
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.004 Å
- R factor = 0.059
- wR factor = 0.130
- Data-to-parameter ratio = 11.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.10 From the CIF: _reflns_number_total 1657 Count of symmetry unique reflns 1688 Completeness (_total/calc) 98.16% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C9H18NO2+·NO3− | F(000) = 504 |
Mr = 234.25 | Dx = 1.302 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 822 reflections |
a = 7.0696 (19) Å | θ = 3.3–21.0° |
b = 12.473 (3) Å | µ = 0.11 mm−1 |
c = 13.555 (4) Å | T = 291 K |
V = 1195.3 (6) Å3 | Plate, colourless |
Z = 4 | 0.50 × 0.40 × 0.30 mm |
Bruker SMART CCD area-detector diffractometer | 1657 independent reflections |
Radiation source: fine-focus sealed tube | 1256 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
φ and ω scans | θmax = 28.1°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −9→9 |
Tmin = 0.951, Tmax = 0.966 | k = −16→13 |
7286 measured reflections | l = −15→17 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0633P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
1657 reflections | Δρmax = 0.25 e Å−3 |
145 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods |
Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. Main FT–IR (KBr plates, cm-1): 3350–2850 (b, s), 1727 (m), 1695 (s), 1528 (m), 1500 (w), 1416 (m), 1384 (versus), 1315 (s), 1236 (m), 1206 (m) and 1152 (w). ESI-MS: m/z 172.1 [C9H17NO2H]+ (100%) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.7780 (5) | 0.8112 (2) | 0.1218 (2) | 0.0459 (7) | |
H1A | 0.8612 | 0.8220 | 0.0648 | 0.055* | |
C2 | 0.8917 (4) | 0.8369 (2) | 0.2179 (2) | 0.0418 (7) | |
C3 | 0.7419 (4) | 0.8922 (2) | 0.2844 (2) | 0.0373 (6) | |
C4 | 0.6235 (5) | 0.9575 (3) | 0.2130 (2) | 0.0513 (8) | |
H4A | 0.4968 | 0.9677 | 0.2388 | 0.062* | |
H4B | 0.6804 | 1.0273 | 0.2022 | 0.062* | |
C5 | 0.6172 (6) | 0.8948 (3) | 0.1177 (2) | 0.0654 (11) | |
H5A | 0.6350 | 0.9424 | 0.0618 | 0.079* | |
H5B | 0.4959 | 0.8592 | 0.1107 | 0.079* | |
C6 | 0.7017 (5) | 0.6995 (2) | 0.1185 (2) | 0.0462 (8) | |
C7 | 0.8165 (6) | 0.9572 (3) | 0.3704 (2) | 0.0593 (9) | |
H7A | 0.7124 | 0.9879 | 0.4060 | 0.089* | |
H7B | 0.8968 | 1.0134 | 0.3461 | 0.089* | |
H7C | 0.8877 | 0.9114 | 0.4136 | 0.089* | |
C8 | 0.9861 (6) | 0.7406 (3) | 0.2650 (3) | 0.0650 (10) | |
H8A | 1.0458 | 0.7620 | 0.3255 | 0.097* | |
H8B | 1.0795 | 0.7121 | 0.2208 | 0.097* | |
H8C | 0.8927 | 0.6867 | 0.2786 | 0.097* | |
C9 | 1.0451 (6) | 0.9177 (3) | 0.1902 (3) | 0.0726 (12) | |
H9A | 1.1126 | 0.9390 | 0.2485 | 0.109* | |
H9B | 0.9877 | 0.9796 | 0.1605 | 0.109* | |
H9C | 1.1313 | 0.8854 | 0.1443 | 0.109* | |
N1 | 0.6150 (4) | 0.80843 (19) | 0.32904 (16) | 0.0445 (6) | |
H1B | 0.5145 | 0.8400 | 0.3559 | 0.067* | |
H1C | 0.6781 | 0.7726 | 0.3753 | 0.067* | |
H1D | 0.5773 | 0.7631 | 0.2823 | 0.067* | |
N2 | 0.2273 (4) | 0.1248 (2) | 0.99836 (17) | 0.0459 (6) | |
O1 | 0.5708 (4) | 0.6693 (2) | 0.16836 (19) | 0.0771 (9) | |
O2 | 0.7874 (4) | 0.63802 (18) | 0.05624 (16) | 0.0652 (7) | |
H2A | 0.7438 | 0.5790 | 0.0651 | 0.098* | |
O3 | 0.3231 (4) | 0.08986 (19) | 1.06495 (16) | 0.0643 (7) | |
O4 | 0.1672 (4) | 0.06448 (18) | 0.93074 (16) | 0.0626 (7) | |
O5 | 0.1874 (5) | 0.22022 (18) | 0.99345 (18) | 0.0761 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0573 (19) | 0.0462 (17) | 0.0342 (13) | −0.0035 (15) | 0.0112 (15) | 0.0009 (12) |
C2 | 0.0392 (16) | 0.0427 (15) | 0.0435 (15) | −0.0007 (14) | 0.0048 (14) | −0.0042 (13) |
C3 | 0.0401 (15) | 0.0344 (14) | 0.0373 (12) | 0.0005 (13) | −0.0015 (12) | −0.0015 (11) |
C4 | 0.063 (2) | 0.0438 (16) | 0.0471 (16) | 0.0108 (16) | 0.0009 (17) | 0.0043 (14) |
C5 | 0.088 (3) | 0.062 (2) | 0.0467 (17) | 0.015 (2) | −0.015 (2) | 0.0025 (16) |
C6 | 0.055 (2) | 0.0498 (18) | 0.0340 (14) | −0.0061 (16) | 0.0036 (16) | −0.0066 (13) |
C7 | 0.069 (2) | 0.0583 (19) | 0.0504 (17) | −0.0030 (18) | −0.0022 (19) | −0.0146 (15) |
C8 | 0.058 (2) | 0.071 (2) | 0.066 (2) | 0.024 (2) | −0.0036 (19) | −0.007 (2) |
C9 | 0.054 (2) | 0.079 (3) | 0.085 (3) | −0.022 (2) | 0.020 (2) | −0.017 (2) |
N1 | 0.0507 (15) | 0.0479 (14) | 0.0350 (12) | 0.0042 (13) | 0.0062 (12) | 0.0004 (11) |
N2 | 0.0493 (15) | 0.0445 (15) | 0.0439 (13) | 0.0038 (13) | −0.0007 (14) | −0.0073 (12) |
O1 | 0.090 (2) | 0.0665 (15) | 0.0747 (16) | −0.0313 (15) | 0.0360 (16) | −0.0288 (14) |
O2 | 0.0814 (18) | 0.0495 (12) | 0.0647 (14) | −0.0117 (12) | 0.0270 (14) | −0.0201 (11) |
O3 | 0.0740 (17) | 0.0661 (14) | 0.0530 (12) | 0.0047 (13) | −0.0223 (14) | −0.0008 (11) |
O4 | 0.0780 (17) | 0.0521 (13) | 0.0577 (13) | 0.0111 (12) | −0.0260 (13) | −0.0216 (11) |
O5 | 0.102 (2) | 0.0509 (14) | 0.0751 (16) | 0.0147 (15) | −0.0264 (17) | −0.0136 (12) |
C1—C6 | 1.495 (4) | C7—H7A | 0.9600 |
C1—C5 | 1.543 (5) | C7—H7B | 0.9600 |
C1—C2 | 1.564 (4) | C7—H7C | 0.9600 |
C1—H1A | 0.9800 | C8—H8A | 0.9600 |
C2—C8 | 1.515 (4) | C8—H8B | 0.9600 |
C2—C9 | 1.528 (5) | C8—H8C | 0.9600 |
C2—C3 | 1.552 (4) | C9—H9A | 0.9600 |
C3—N1 | 1.504 (4) | C9—H9B | 0.9600 |
C3—C7 | 1.515 (4) | C9—H9C | 0.9600 |
C3—C4 | 1.517 (4) | N1—H1B | 0.8900 |
C4—C5 | 1.511 (5) | N1—H1C | 0.8900 |
C4—H4A | 0.9700 | N1—H1D | 0.8900 |
C4—H4B | 0.9700 | N2—O3 | 1.210 (3) |
C5—H5A | 0.9700 | N2—O5 | 1.225 (3) |
C5—H5B | 0.9700 | N2—O4 | 1.259 (3) |
C6—O1 | 1.206 (4) | O2—H2A | 0.8068 |
C6—O2 | 1.291 (3) | ||
C6—C1—C5 | 111.3 (3) | O1—C6—C1 | 123.4 (3) |
C6—C1—C2 | 113.7 (2) | O2—C6—C1 | 113.8 (3) |
C5—C1—C2 | 105.7 (2) | C3—C7—H7A | 109.5 |
C6—C1—H1A | 108.7 | C3—C7—H7B | 109.5 |
C5—C1—H1A | 108.7 | H7A—C7—H7B | 109.5 |
C2—C1—H1A | 108.7 | C3—C7—H7C | 109.5 |
C8—C2—C9 | 108.3 (3) | H7A—C7—H7C | 109.5 |
C8—C2—C3 | 114.1 (2) | H7B—C7—H7C | 109.5 |
C9—C2—C3 | 109.5 (3) | C2—C8—H8A | 109.5 |
C8—C2—C1 | 114.5 (3) | C2—C8—H8B | 109.5 |
C9—C2—C1 | 107.2 (3) | H8A—C8—H8B | 109.5 |
C3—C2—C1 | 103.0 (2) | C2—C8—H8C | 109.5 |
N1—C3—C7 | 105.7 (2) | H8A—C8—H8C | 109.5 |
N1—C3—C4 | 107.5 (3) | H8B—C8—H8C | 109.5 |
C7—C3—C4 | 113.3 (2) | C2—C9—H9A | 109.5 |
N1—C3—C2 | 109.4 (2) | C2—C9—H9B | 109.5 |
C7—C3—C2 | 116.5 (3) | H9A—C9—H9B | 109.5 |
C4—C3—C2 | 104.1 (2) | C2—C9—H9C | 109.5 |
C5—C4—C3 | 106.5 (2) | H9A—C9—H9C | 109.5 |
C5—C4—H4A | 110.4 | H9B—C9—H9C | 109.5 |
C3—C4—H4A | 110.4 | C3—N1—H1B | 109.5 |
C5—C4—H4B | 110.4 | C3—N1—H1C | 109.5 |
C3—C4—H4B | 110.4 | H1B—N1—H1C | 109.5 |
H4A—C4—H4B | 108.6 | C3—N1—H1D | 109.5 |
C4—C5—C1 | 107.3 (3) | H1B—N1—H1D | 109.5 |
C4—C5—H5A | 110.3 | H1C—N1—H1D | 109.5 |
C1—C5—H5A | 110.3 | O3—N2—O5 | 121.3 (3) |
C4—C5—H5B | 110.3 | O3—N2—O4 | 121.1 (3) |
C1—C5—H5B | 110.3 | O5—N2—O4 | 117.6 (3) |
H5A—C5—H5B | 108.5 | C6—O2—H2A | 105.4 |
O1—C6—O2 | 122.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O4i | 0.89 | 2.02 | 2.897 (3) | 166 |
N1—H1B···O5i | 0.89 | 2.47 | 3.109 (4) | 130 |
N1—H1C···O3ii | 0.89 | 2.42 | 3.113 (3) | 135 |
N1—H1C···O5ii | 0.89 | 2.12 | 2.992 (4) | 166 |
N1—H1D···O1 | 0.89 | 1.94 | 2.802 (3) | 163 |
O2—H2A···O4iii | 0.81 | 1.87 | 2.671 (3) | 171 |
C5—H5B···O1 | 0.97 | 2.55 | 2.914 (5) | 102 |
Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) −x+1, y+1/2, −z+3/2; (iii) x+1/2, −y+1/2, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register